1-Butanol → HCID 22989217, compound

HRID 1169038Notes

Reaction equation

HRID 1169038 reaction equation
[C:1]([C:5]1[N:13]=[C:12]2[N:7]([N:8]=[C:9](Cl)[CH:10]=[CH:11]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:15]1([CH:21]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][NH2:32])[CH2:25][CH2:24]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)C(C)C)C.[C:48](=[O:51])([O-:50])O.[Na+].C([OH:57])CCC>>[C:21]([OH:57])(=[O:22])/[CH:33]=[CH:38]/[C:48]([OH:50])=[O:51].[C:1]([C:5]1[N:13]=[C:12]2[N:7]([N:8]=[C:9]([NH:32][CH2:31][CH2:30][CH2:29][N:26]3[CH2:25][CH2:24][CH:23]([O:22][CH:21]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:28][CH2:27]3)[CH:10]=[CH:11]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 108784452-tert-Butyl-6-chloro[1,2,4]triazolo[1,5-b]pyridazineHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamine

Product 1

HCID 22989217HCID 22989217, compound

Procedure

276 mg of 2-t-butyl-6-chloro[1,2,4]triazolo[1,5-b]pyridazine and 0.425 g of 4-(diphenylmethoxy)-1-piperidinepropanamine were suspended in 8 ml of 1-butanol; 0.45 ml of N-ethyldiisopropylamine was added, followed by heating and refluxing for 40 hours. Ice water and sodium hydrogen carbonate were added, followed by extraction with ethyl acetate; the extract was washed with saturated saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (50:5:1). The desired fraction was collected and concentrated; the residue was dissolved in 10 ml of ethyl acetate; a solution of 40 mg of fumaric acid in 5 ml of methanol was added, followed by concentration. The residue was powdered by the addition of ethyl ether, filtered and collected to yield 164 mg of the title compound.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 40 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe extract was washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with ethyl acetate:methanol:triethylamine (50:5:1)
  8. customThe desired fraction was collected
  9. concentrationconcentrated
  10. dissolutionthe residue was dissolved in 10 ml of ethyl acetate
  11. additiona solution of 40 mg of fumaric acid in 5 ml of methanol was added
  12. concentrationfollowed by concentration
  13. additionThe residue was powdered by the addition of ethyl ether
  14. filtrationfiltered
  15. customcollected

Sources & evidence

ORD record
ord-99c1388594b64ed1a2f39d189c180711
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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